Functionalized Calixarenes: New Applications as Catalysts, Ligands, and Host Molecules

Shinkai, Seiji

doi:10.1007/978-94-009-2013-2_7

Cited by 29 publications

(13 citation statements)

References 67 publications

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“…It has been thought that this high selectivity of 2a for Na + against K + is due to the appropriate size of 2a, which have a cavity size adjusted to that between Li + and Na + . It is in agreement with our previously reported study [33] [36] and by literature [37]. Nevertheless dibutyronitrile derivative of this compound (3a) was selective for Cs + ion as well as Na + ion.…”

Section: Extraction Studiessupporting

confidence: 93%

Synthesis and Extraction Studies of Calix[4]-Crown-4 Oxime Derivatives

Akkuş¹,

Aslan²

2017

IJOC

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The article comprises synthesis of calyx[4]-oxa-crown, and calix[4]-thia-crown compounds containing nitrile groups (3a, 3b) and amino groups (4a, 4b) and their corresponding oxime derivatives (5a, 5b) and liquid-liquid extraction studies of these compounds. The oxime derivatives of compounds (5a, 5b) have been synthesized by reacting of di-n-butylamino derivatives of calix[4]-oxa-crown, and calix[4]-thia-crown compounds (4a, 4b) with amphi-chloroglyoxime in methanol-THF. Their cation and anion transfer studies were performed by using liquid-liquid extraction procedure. It has been concluded from the observations that the compound 3a shows a good extraction behavior toward Na + ion in the presence of other metal cations. Whereas, its oxime derivatives transfers all of the metal cations used in the liquid-liquid extraction studies.

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Section: Extraction Studiessupporting

confidence: 93%

Synthesis and Extraction Studies of Calix[4]-Crown-4 Oxime Derivatives

Akkuş¹,

Aslan²

2017

IJOC

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“…Consistent with the solvent study, the broad signals of 14 also suggest that it may self-associate into oligomeric types of structures such as G-ribbons or G-quartets (36,41). The self-assembly of cytosine-calix [4]arene (13) could not be clearly identified due to the lack of amino proton signals even at lower temperatures.…”

Section: Self-assembly Of Nucleobase-calix[4]arenessupporting

confidence: 64%

“…A signature signal occurring at 30-31 ppm should be observed when neighbouring aromatic rings are oriented to the same side to yield a cone conformation. Following this simple rule, we conclude that all four synthesised calix [4]arenes (11)(12)(13)(14) adopt a cone conformation (Supplementary Information, available online). The inner cavities of calixarenes with a pre-organised cone conformation allow them to accommodate molecules with matching sizes.…”

Section: Synthesis Of Calix[4]arenes Containing a Single Nucleobasementioning

confidence: 89%

“…Cu(I) warrants the formation of the 1,4-regioisomer of 1,2,3-triazole. All the synthesised nucleobase-calix [4]arenes (11)(12)(13)(14) showed good solubility in common organic media.…”

Section: Synthesis Of Calix[4]arenes Containing a Single Nucleobasementioning

confidence: 99%

“…Calixarene derivatives have been used in nuclear waste treatment owing to their high selectivity for caesium and uranium ions (11). The selectivity of calixarenes for alkali, alkaline earth and transition metal ions has led to the development of cation-selective electrodes, optical sensors, artificial enzyme models and novel catalysts for organic reactions (12,13). Chiral calixarenes (14) have also been developed for distinguishing between enantiomers -one of the most difficult tasks for molecular recognition.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of nucleobase-calix[4]arenes via click chemistry and evaluation of their complexation with alkali metal ions and molecular assembly

Liu

Minier

Franz

et al. 2011

Supramolecular Chemistry

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In this study, calix[4]arene derivatives (11 -14) bearing a single nucleobase (adenine, thymine, cytosine or guanine) were synthesised via click chemistry. The complexation ability of the synthesised derivatives with alkali metal ions was measured using MALDI-TOF mass spectrometry, and their molecular assembly in CDCl 3 was determined using 1 H NMR. Calix[4]arene derivatives (11 -14) formed 1:1 complexes with all alkali metal ions and the rank order for the complexation selectivity was Rb þ . Cs þ . K þ ø Na þ . Li þ . The attachment of nucleobase at the upper rim of calix[4]arene had little effect on its complexation selectivity for alkali metal ions. Thymine-, adenine-and guanine-calix[4]arenes formed selfassembled structures in CDCl 3 via base-base interactions. In addition, adenine-calix[4]arene (11) bound to thyminecalix[4]arene (12) to form a discrete species via Hoogsteen hydrogen bonding.

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Finessen mit Schwefel: Calixarene als Uranophile

Asfari¹,

Bilyk

Dunlop

et al. 2001

Angew. Chem.

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Hinweise darauf, dass mit Donoratomen versehene Calixarene als selektive Liganden für U VI (in Form von UO 2 2 ) dienen könnten, [1] haben das Interesse an den Koordinationsmodi von Uran in solchen Spezies geweckt. [2] In frühen Arbeiten [3, 4] über die Synthese von UO 2 2 -spezifischen Liganden, so genannten ¹Uranophilenª, [5,6] nahm man angesichts der Tatsache, dass für UO 2 2 -Komplexe übliche Geometrien für andere Metallionen kaum bekannt sind, [7] an, dass Liganden mit im Wesentlichen planaren pentagonalen oder hexagonalen Donoratomanordnungen am geeignetsten sind. Dieses Konzept [1] diente auch als Erklärung für die selektive Bindung von UO 2 2 durch eine Reihe von (wasserlöslichen) Calix[6]arenen, wobei bei dieser Betrachtung allerdings mehr die Geometrie, denn die Abmessungen der Donoratomanordnung und die Art der Donoren im Mittelpunkt standen. Der Vorschlag, dass hier möglicherweise sechs Phenoxiddonoren beteiligt sind, scheint von der allgemein bekannten Koordinationschemie von UO 2 2 mit Alkoxidliganden abzuweichen, [8] denn bislang wurden nur nahezu oktaedrische Spezies mit vier solcher Liganden gefunden. U VI -Alkoxide [U(OR) 6 ] sind zwar bekannt, [8] aber sie sind nicht unter den Bedingungen stabil, unter denen Uranylionen/Calixaren-Komplexe durch Lösungsmittelextraktion hergestellt werden, wenngleich sich derartige Spezies mit einem Calix[6]arenliganden in seltenen Fällen bilden können. Bemerkenswerterweise ergab die Strukturaufklärung eines Pyridin-stabilisierten U VI -Derivates von p-tBu-Calix[6]aren, [9] dass für eine oktaedrische Koordination zwei Ligandmoleküle benötigt werden, die beide als dreizähnige Donoren in einer 1,2,3alternate-Konformation fungieren. In Kristallstrukturen von UO 2 2 -Komplexen mit Calixarenen, die ausschlieûlich Phenoxiddonoren enthalten, koordinieren maximal vier Phenoxidgruppen, die die äquatorialen [*] Prof.

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Functionalized Calixarenes: New Applications as Catalysts, Ligands, and Host Molecules

Cited by 29 publications

References 67 publications

Synthesis and Extraction Studies of Calix[4]-Crown-4 Oxime Derivatives

Synthesis and Extraction Studies of Calix[4]-Crown-4 Oxime Derivatives

Synthesis of nucleobase-calix[4]arenes via click chemistry and evaluation of their complexation with alkali metal ions and molecular assembly

Finessen mit Schwefel: Calixarene als Uranophile

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